How many articles, books, and webinars have you consumed about the best way to do big-picture planning? Have you noticed that they all say contradictory things?
One says you should plan out 5 years, then 3 years, then 1 year, then the quarter. Another says to just focus on your one next step.
One says you should set really ambitious targets. Another says you should give yourself the chance to experience small wins. Yet another says you should only measure backwards.
Here’s what I believe: none of them are wrong. Different approaches work differently for different leaders, businesses, and contexts. No matter what, though, big-picture planning is worth doing. And it’s worth finding what feels supportive for you.
Over the past 8 years, I’ve refined a system that works for my personality. I’m going to share it with you so you can grab any elements that resonate and bake them into your own pie.
Here’s the video version of what’s written below if you want to see this in real life!
Why Planning Actually Matters
Why does big-picture planning matter, anyways? What outcome are we looking for?
Here’s what a solid plan does for me:
- It gives me a lighthouse to move towards rather than being reactive to the moods or needs of today
- It reminds me of why I’m running this business in the first place
- It helps me focus on a few major priorities instead of trying to fix and do everything at once
- It helps me achieve bigger projects and see meaningful progress when I look back on the year
My Strategic Framework
I set up a dashboard in Notion with five core elements. Each one works together to give me a sense of structure throughout the year.
1. Foundation
When I’m in the thick of a normal Tuesday, it’s easy to plow through calls and tasks without feeling much meaning in any of it. I believe, though, that work is deeply meaningful – it’s part of being human, and part of how we contribute to goodness in the world.
Sometimes, when our divided political environment gets me overwhelmed, I start looking around at all of the signs of human collaboration around me. I see a plane overhead and think about the thousands of people over generations who have worked together to give us a gift like that. Obviously, so much is broken, but there’s also a complete stranger out there somewhere who took a gorgeous picture of a sloth and then dropped it into the Internet (another marvel of humans working hard together). My desktop is less boring because of it, and I’m grateful.
The foundation section of my dashboard is meant to remind me of the deeper meaning I want to give to my own work.
Purpose: Our is “Honoring operators, unleashing visionaries”. It defines why Smooth Operator exists instead of me pursuing something easier.
Success Definition: I like the question, “I’m being successful when…” It helps me avoid this ever-moving target of “I’ll be successful after I achieve….” For me, success feels like deposits into the bank of meaning, family coming first, safety and stability, and clients and team members staying long-term. I don’t have to be rich or famous for these things. I can have them now.
Core Values: A lot has been said about defining values, and I don’t pretend to be an expert in that space, but the ones that are resonating for me right now are shalom (cultivating wholeness and thriving), making order out of chaos, and courage.
Word of the Year: This is one word that captures the energy I want to bring to the year. Pro tip: choose something you can control – I learned this when my “fun” year became massively un-fun. My 2025 word is “meaning,” which I like much better.
2. Annual Targets: Focusing on What I Can Control
Here’s where I diverge from traditional goal-setting advice. I only set targets for things that are 100% within my control.
I used to set revenue goals and client targets, but it felt awful when external factors affected results, even when I’d executed perfectly. Action-based targets allow me to “fully win” regardless of market conditions.
These might include:
- Writing a book
- Maintaining specific marketing activities consistently
- Planning an event
- Following through on operational improvements
Interestingly, despite not having outcome-based targets this year, we’re on track for a record revenue year. Focusing on what I can control has been more effective for me than stressing about what I can’t.
3. Core Vital Need: The One Thing That Matters Most
I learned this concept from Mike Michalowicz’s “Fix This Next” – the idea that businesses have a hierarchy of needs, just like people. When you’re stranded on a desert island, your priorities are crystal clear: water, shelter, food. You’re not worried about the small scratch on your leg. In a business, the same can be true. What’s the ONE thing that matters most?
I always want to remember our core vital need – the one thing that, if I nail it, will have the biggest impact on everything else. This way, I can make sure I’m focusing most of my problem-solving energy on that one thing instead of trying to solve all the things.
4. The “Big Three Projects” Rule
As entrepreneurs, we’re constantly generating ideas. This is an amazing gift, but can easily turn into dozens of brilliant concepts sitting half-finished on the back burner.
I limit myself to three major projects at any time. I cannot start a new big project until one of these is completed or consciously set aside.
Giving myself a constraint like this allows me to experience the momentum and satisfaction that comes from completing meaningful work. It takes some getting used to because you’re giving up some of the freedom that comes with having an idea in the morning and starting on it in the afternoon. But the balance between freedom and constraint is one of the core polarities of the universe, and many of us entrepreneurs are a bit imbalanced on that front. Too much freedom in your business may feel nice in the moment, but it will keep you in a project graveyard of open loops and good ideas that never became anything real.
5. Six-Week Sprints
Mapping out a granular annual plan has never worked for me. In January, deciding what specific project I should work on in August can feel like trying to be a psychic.
Instead, I use six-week sprints. I can make meaningful progress in that amount of time, but it’s short enough for me to be a bit more realistic about what I can do and what other things are going on. I’m more likely to accommodate a one-week vacation, the first week of school, or other life things in my expectations.
Each time I start a new sprint, I can pull projects off of my Ideas list (which I keep separate from my to-do list) and pivot based on what happened in the past sprint without losing sight of my annual targets.
To make the math easy, I provide 2 months of time for each 6-week sprint. Then I get a bonus week (or two) for things inevitably taking longer than I expected, and a week to reflect and plan for the next one.
Each sprint includes:
- The major next steps for my Big Three projects (broken out into 1-2 hour chunks of work)
- 4-6 smaller projects (things I can knock out in 2 hours or less)
- Built-in buffer time for inevitable delays (week 7)
- A reflection week to debrief and plan the next cycle (week 8)
Once I’ve mapped out the sprint, I’ll set up tasks in my to-do list and spread them out over the next six weeks. Then, when I plan each week, I already know what I should be doing to stay on track.
I print out my sprint plan and keep it on my desk as a visual reminder. If it only lives in a digital tool, I’ll never reference it again.
Protecting My To-Do List
I’m surprisingly protective about what makes it onto my active to-do list. It only contains:
- Current Big Three projects
- Recurring activities (mainly marketing and admin tasks)
- Client delivery work
- A few small random tasks that crop up
Everything else goes on a separate “Ideas” list. This prevents the soul-crushing experience of a to-do list that grows faster than I can complete things.
I lived with 75-item daily to-do lists for years after starting my business, and it was miserable. This approach actually lets me feel like I’m winning.
The Power of Reflection
At the end of each sprint, I take time to evaluate:
- What worked well? What didn’t?
- What should I cut, delegate, or streamline?
- What energized me? What drained me?
- What did I learn?
- Is everything still aligned with my values and annual targets?
Building reflection into the system helps me avoid going too hard into ‘workhorse mode,’ where I’ll just get stuff done without sitting back to celebrate my progress or reflect on what I’m learning.
Why This System Works
This approach works for me for a few reasons. It:
- Prevents overwhelm by keeping my to-do list realistic
- Keeps me focused without locking me into a rigid plan
- Creates momentum because I’m noticing the projects I’m completing and putting more energy behind each one
- Helps me be proactive instead of just reacting to what others are asking of me
- Gives me the chance to win
More than anything, I want to feel like I’m making progress. I want to sit down every morning with a clear and realistic picture of what I should be doing, and I want to wrap up every day feeling like I accomplished what I set out to do. This system gives me that.
Remember, the best planning system is one you’ll consistently use. Take what resonates from this approach, adapt it to your personality and business needs, and commit to testing it for several cycles before making major modifications.
Ask yourself: what’s one element of this planning system I could try on this week? I’d love to hear how you balance having great ideas with actually finishing projects.
